Rawle Hollingsworth
Professor Office: 116 Biochemistry
Phone: 517-353-0613 /
Websites: Area
Awards & Honors
Genealogy/Graduates
Chemistry of Life Processes
(Research Description PDF - 1112 kb)In our laboratory, we are interested in organic synthesis especially of optically active targets and targets of biological significance and in the development of synthetic strategies and intermediates. We are also interested in the preparation of self-assembling systems, supramolecular assemblies and advanced materials with novel optical, electronic and magnetic properties. Other traditional areas of strength for us are the applications of modern spectroscopic and physicochemical methods to problem-solving in the biological sciences, the structural analyses of complex glycoconjugates, molecular mechanisms of biological phenomena and calculation and simulation of the structure and properties of biomolecules and related molecular ensembles. Among our recent accomplishments is the traditional organic synthesis area is the development of routes to optically active intermediates for use in the synthesis of a variety of drugs and advanced materials using carbohydrates as chiral raw materials. This chemistry is being practiced around the world on a commercial scale. These intermediates have been integrated into syntheses of anti-virals, cholesterol-lowering drugs, membrane probes and mimics, carnitine and GABOB to name a few. The regulation of carbohydrate and nucleic acid processing, glycosylation and glycosidases is another area of interest to us and we have a large effort in the preparation of glycosidase and glycosyl transferase inhibitors aimed at developing drugs for cancer, autoimmune diseases and antimicrobials. An example of a rearrangement used for the preparation of glycosidase inhibitors is shown at top left. A new ring system that can be used for glycosidase inhibition is shown below to the left.
Selected Publications
General Three Carbon Chiral Synthons from Carbohydrates: Chiral Pool and Chiral Auxiliary Approaches, R. I. Hollingsworth and G. J. Wang, Carbohydrate Synthons In Natural Products Chemistry: Synthesis, Functionalization And Applications, 2003 841, 85.Remote Site Bromination via a Cascade Rearrangement Involving Two Bridging Dioxonium Species During Oxidative Cleavage of a Benzylidene Acetal, X. Z. Song and R. I. Hollingsworth, Carbohydrate Research 2003, 338(4), 369.
Offsetting of the Tubule-Forming Tendency of Chiral Diacetylene-Containing Lipids: Planar Strips, Ribbons and Liposomes from a Diacetylenic Lipid Analog of a Thermophilic Bacterium, G. Wang and R. I. Hollingsworth, Advanced Materials 2000, 12, 871.
A Simple 3-Step Method for Preparing Protected Optically-active Hydroxymethyl Oxazolidinones from Optically-active 3-Hydroxy-butyrolactones, G. Wang and R. Hollingsworth, Tetrahedron Asymmetry 2000, 11, 4429.
Synthesis, Conformational Analysis and Phase Characterization of a Novel Glycolipid with a Chiral Spiral Acetal Linkage, J. Song and R. Hollingsworth, J. Amer. Chem. Soc. 1999, 121, 1851.
